Assignment of the 1H, 19F, and 13C NMR spectra of 2-deoxy-2-fluoro-d-ribose and characterisation of the isomeric equilibrium
| Autor: | R. Duncan Farrant, Paul N. Sanderson, John C. Lindon, B. C. Sweatman |
|---|---|
| Rok vydání: | 1996 |
| Předmět: |
chemistry.chemical_classification
Deuterium NMR Carbon-13 NMR satellite Stereochemistry Organic Chemistry Nuclear magnetic resonance spectroscopy of nucleic acids General Medicine Carbon-13 NMR Furanose Biochemistry Analytical Chemistry NMR spectra database Pyranose chemistry Conformational isomerism |
| Zdroj: | Carbohydrate Research. 284:51-60 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/0008-6215(96)00020-1 |
| Popis: | The assignment of the 1 H, 19 F, and 13 C NMR chemical shifts and coupling constants of 2-deoxy-2-fluoro- d -ribose, an important intermediate in the synthesis of antiviral nucleoside drugs, is reported and the NMR spectra are used to determine the proportions of the pyranose and furanose forms together with the anomeric ratios in acetone- d 6 solution. The β-pyranose isomer is shown to exist at equilibrium with both 4 C 1 and 1 C 4 conformations in approximately equal proportions in fast exchange. The α-pyranose isomer at equilibrium is predominantly in the 4 C 1 form but the 1 C 4 conformer is also present in solution, the two forms being in intermediate exchange on the 19 F NMR timescale but in fast exchange on the 1 H and 13 C NMR timescales. For both the pyranose and furanose forms, the β-anomer predominates. The results are similar to those for d -ribose. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect